Draw the major product(s) of the following reactions including stereochemistry when it is appropriate. CH₂CH₂-CEC-CH₂CH3 + 1 Br₂ • Consider E/Z stereochemistry of alkenes. • If there is more than one major product possible, draw all of them. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. ●

Draw the predominant product(s) of the following reactions including stereochemistry when it is appropriate. CH3CH2-CEC-H 1 HI • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. P opy aste ChemDoodle Submit Answer Retry Entire Group 5 more group attempts remaining

Draw the predominant product(s) of the following reactions including stereochemistry when it is appropriate. CH₂CH₂ CH₂-C=C-H + 1 HI • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu.

Draw the organic product(s) of the following reactions, and include carbon dioxide if it is produced. KMNO4 / H3O* CEC-CH2CH2CH2-C • You do not have to consider stereochemistry. If a compound is formed more than once, add another sketcher and draw it again. Draw carbon dioxide in its own sketcher if it is produced. Separate multiple products using the + sign from the drop-down menu. If no reaction occurs, draw the organic starting material.

Draw the major product(s) of the following reactions including stereochemistry when it is appropriate. -CEC-H + 1 Br2 • Consider E/Z stereochemistry of alkenes. • If there is more than one major product possible, draw all of them. • Draw one structure per sketcher. Add additional sketchers using the drop- down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu.

[References] Draw the organic product(s) of the following reactions, and include carbon dioxide if it is produced. 0 ● H3C-CEC-H You do not have to consider stereochemistry. • If a compound is formed more than once, add another sketcher and draw it again. • Draw carbon dioxide in its own sketcher if it is produced. Separate multiple products using the + sign from the drop-down menu. • If no reaction occurs, draw the organic starting material. + [... ? KMnO4 / H3O+ ChemDoodle ▼n [] Previous

Draw the major product(s) from addition of HBr to the alkene below. H3C H3C • You do not have to consider stereochemistry. • If there is more than one major product possible, draw all of them. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. + SAVIL ? ChemDoodle Ⓡ Sn [F

Draw a structural formula for the major organic product of the reaction shown. CH;CH2 c=c HBr H CH3 • You do not have to consider stereochemistry. • If there is more than one major product possible, draw all of them. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. opy aste ... ChemDoodle

Draw the product(s) of the following reactions. HOCH₂-CEC-(CH₂)7-C . OCH3 H₂ Lindlar catalyst • Consider E/Z stereochemistry of alkenes. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu.

Draw structural formulas for the products of the reaction shown below. CH3CH₂-O-CH₂CH3 + HI • You do not have to consider stereochemistry. Assume equimolar amounts of the reagents. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. ? ChemDoodleⓇ ▼n [F <